3-Amino-1,2-propanediol → HCID 11565094, compound

HRID 2397426Notes

Reaction equation

HRID 2397426 reaction equation
O=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[OH:13][CH:14]([CH2:17][OH:18])[CH2:15][NH2:16].[H][H]>O.CO.[Ni]>[OH:13][CH:14]([CH2:17][OH:18])[CH2:15][NH:16][CH2:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4]

Participants

7

Reactant 3

HCID 735613-Amino-1,2-propanediolHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 178418361HCID 178418361, compound

Product 1

HCID 11565094HCID 11565094, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 19.6 gm (0.2 mol) of D-glucose (containing 0.1 mol of H2O) and 18.2 gm (0.2 mol) of 2,3-dihydroxypropylamine in 400 ml of water and 350 ml of methanol was, after the addition of 18 gm of Raney nickel, hydrogenated for 2 hours at 50° C. in an autoclave having stirring means, and then for 3 hours at 70° C., both at a hydrogen pressure of about 180 kg/cm. After the catalyst had been filtered off and the solvent removed by distillation under reduced pressure, the residue was recrystallized from water/2-propanol and digested with cold 2-propanol. 36.5 gm (72% of theory) of colorless, crystalline N-(2,3-dihydroxypropyl)-glucamine with a melting point of 133° to 134° C. was obtained.

Workup

  1. waitfor 3 hours at 70° C.
  2. filtrationAfter the catalyst had been filtered off
  3. customthe solvent removed by distillation under reduced pressure
  4. customthe residue was recrystallized from water/2-propanol

Sources & evidence

ORD record
ord-4a67fcced24149a6bfdd0afc1fbdfdc5
Source dataset
uspto-grants-1977_05
Patent number
US04021539

Reaction notes

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